During ESPN days, Jemele Hill ‘canceled’ dates if men brought up Stephen A. Smith or Skip Bayless

Jemele Hill had a hard line back when she was on the dating scene.

When Hill (who was married in 2020) was still a star columnist and commentator at ESPN, there were two personalities who she would not talk about on dates: Stephen A. Smith and Skip Bayless.

Hill brought the rule up in an appearance on The Dan Le Batard Show with Stugotz coming off a weekend in which Project Veritas founder James O’Keefe III released audio of an alleged ESPN producer painting Smith as a racial caricature during a social situation with a woman.

Hill called the secret recording “despicable” before revealing how she would have avoided it herself.

“It…kind of reminds me of a rule I used to have when I was dating,” Hill said.

“A long, long time ago when I was a single woman out here in the wild of dating, I had a rule that if I was on a date with somebody or in that kind of initial interaction where it’s like, ‘OK this guy’s cute,’ there’s some level of flirting that’s going on. If they ask me about Stephen A. Smith or Skip Bayless, immediately that dude was canceled. Immediately. Like no, I don’t want anything to do with you.”

Of course, when Hill was first coming up at ESPN, the two First Take stars were big names. As any week of Awful Announcing coverage will show, there is unending interest in both men’s personas and opinions.

It would be natural for a man Hill dated to be curious about Smith and Bayless. But of course, from her end, it illustrated the type of celebrity chasing that the ESPN producer in O’Keefe’s clip fell victim to. That line of questioning also signaled a complete lack of interest in the actual date.

“There is nothing more unsexy and unflattering than when you’re talking to somebody who’s a potential love interest and you’re … trying to get to know them and they’re like, ‘so what’s Stephen A. Smith like?'” Hill laughed. “Like, do you want to be on a date with Stephen A. Smith? Because this is doing nothing for me. Whatever arousal point I had in this conversation just immediately went to negative.”

Working at ESPN is a cool job. But it’s easy to imagine where a date would veer off course from a romantic night out into a game of “20 Questions” about all things Bristol.